As part of The Drum’s Rebel 50, powered by WeTransfer Advertising, where we list the 50 boldest and brashest marketers from around the world, two marketing leaders took to The Drum Live stage to unpack what it really means to be rebellious.
For Anders Braso, chief marketing officer at Monocle magazine and one of our Rebel 50, rebellion is about discipline, not chaos. For Berit Block, head of marketing at WeTransfer, it’s about remembering your creative roots and supporting a community that thrives when the rules are bent.
Together, their perspectives highlight how rebellion isn’t about rejecting everything; it’s about knowing what to reject, what to double down on and when to zag while everyone else zigs.
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Braso has little time for the industry’s herd mentality. For him, rebellion begins with the refusal to chase short-term metrics or adopt every new channel just because it exists. “Being a rebel, to me, essentially means parking the industry playbook. It means not necessarily following the herd. So, when people go that way, perhaps you go the other way or in that direction. It’s not about chasing clicks; it’s not about chasing short-term wins. I think, at the end of the day, it is about giving your audience credit and not dumbing down,” he tells The Drum Live audience.
That sense of conviction is why Monocle has taken such a contrarian path since its launch in 2007. While most publishers pivoted away from print over a decade ago, Braso doubled down. While others scrambled for digital-first strategies, he built cafes, shops, radio stations and conferences – physical spaces where the brand’s audience could engage deeply with its worldview.
“Last year was our best year to date,” he says, “and this year so far is the best in Monocle’s history. When a lot of people were moving out of print, for various reasons, we doubled down. When a lot of people went all digital, we launched radio. And in addition, we then opened a number of shops and cafes. Of course, on one hand, these are shop windows, but it’s about more than that. It’s marketing through presence, through community and through hospitality.”
The result is a brand that scales slowly, but with an enviable depth of engagement. Today, Monocle has around 120 staff, 60 correspondents, a thriving events business and three cafes across Europe, all rooted in the belief that real relationships matter more than fleeting clicks. And over and above the 10 annual issues of Monocle magazine that he’ll publish (on four different paper stocks), he’ll print a further 15 publications – so, who says print is dead?
Rebellion, Braso argues, isn’t about recklessness. Paradoxically, it’s actually about discipline: “Just because you have the tools, you don’t necessarily need to use them and you don’t need to be in channels that apply to you just because they exist. It’s about having a little bit of discipline when it comes to – and perhaps also confidence in – your mission and who you are and then taking risks in a disciplined way.”
That approach explains Monocle’s unusual stance on social media. Unlike almost every other publisher, the brand has opted out of the biggest platforms, instead investing in events, salons and conferences where connections are more human and tangible.
“It sounds like we’re anti-social, but we’re actually not,” he says. “The kind of social we believe in involves you with a glass of wine, perhaps, meeting other readers and editors of the magazine face to face. We’re not on Facebook, Instagram or TikTok. Audience growth might take a little longer, but we’re not chasing one-night stands. We’re investing in real relationships.”
If Monocle embodies rebellion through contrarian discipline, WeTransfer embodies it through its origins. Block reminds the audience that the file-sharing giant didn’t begin as a tech startup, but as a workaround built by creatives.
“Not many people actually know where WeTransfer came from. People often assume it’s a US company, but it actually has roots in the Netherlands and was founded by creatives. They were sick and tired of sending couriers around the city, so they came up with the solution for their own creative agency – and it grew from there,” she says.
That origin story gave WeTransfer a rebellious spirit that still shapes its brand and marketing today. Its advertising inventory, for example, was treated not simply as space to be sold, but as a canvas.
“They decided to have the transfer window, which is basically the utility, the service, but everything around it they decided was a canvas, like in the art world. They actually gave that canvas away to friends, to artists, but also to brands because the inventory was definitely not selling out fully at the start.”
That instinct to use marketing real estate for creativity rather than simply chasing programmatic efficiency remains central to the company’s brand positioning today.
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Block believes rebellion also means ensuring marketing isn’t joyless: “I love injecting a bit of fun, a lot of emotion into marketing and WeTransfer has been doing that for a long time,” she says. “We collaborate with a lot of artists, so we have an in-house editorial team, WePresent, an editorial arts platform. We’ve always stayed connected to our community, which I think is important. We take risks and support artists that no one has ever heard of. We fund their projects. So, we also add value to that community, which is an important component.”
That community-first model is what elevates WeTransfer from utility to brand. It gives the company cultural currency with creative audiences and ensures it plays in spaces where it has credibility.
Both marketers agree that taking risks is central to rebellion, but those risks need purpose.
“You need to take a gamble when playing it safe means you’re going to be invisible,” says Braso. “Risk-taking shouldn’t just be a strategy in itself – it needs to be embedded in the DNA of the business.”
Block adds that rebellion also depends on context. “If you’re a marketer who is really high risk-taking, but you operate in an environment where that’s not appreciated, then it’s not worth forcing it. It’s about being in the right environment. Having founders involved in the business can make it easier to stick to principles and not chase short-term profit,” she said, recalling WeTransfer’s decision to reject cluttered display ads in favor of full-screen formats that honored creativity.
Asked which other brands embody rebellion, both leaders point to marketers who blend heritage with originality, with Braso saying: “I want to give a shout out to Charlie Smith, the CMO of Loewe [one of our Rebel 50]. What he’s doing is extraordinary – making a very rich heritage brand incredibly relevant today. Another is Duolingo [CMO Manu Orssaud is also on our Rebel 50 list]. There’s real risk-taking in their communication and product. That kind of brand distinctiveness is incredibly important.”
Block adds Tony’s Chocolonely and insurer Cuvva to her list. “Tony’s is brilliant because it didn’t just focus on promotion; it built its rebellion into the product itself. The chocolate chunks are uneven to represent inequality in the cocoa industry. That’s such a clever integration of product and marketing. Cuvva, too, has used broken out-of-home and upside-down posters to inject fun into a traditionally joyless category,” she notes.
The pair diverges on the role of AI in their marketing strategies. For Braso, authenticity is paramount: “AI is a great tool, but it is not a strategy. No content in Monocle is produced with AI. No photography, no illustrations. There is real human care that goes into the product. You can’t replicate curiosity, taste, serendipity and surprise with AI.”
Block, by contrast, is more open to experimentation: “From a personal perspective, I’m super curious. It’s not going away, so I’m in the fully embracing stage. But for businesses, there’s no point deploying it if there isn’t a real use case. It has to be applied only where it adds value.”
What unites both marketers is a belief that rebellion should mean more than provocation. It should serve a cause, whether that’s protecting journalism, creating spaces for real-world connection or amplifying artists’ voices.
As Block puts it: “I love the concept that marketers can do good and they can drive change. More and more we need it in today’s world – that people don’t just rebel for the sake of it, but they rebel for a cause, to change something for the better.”
In celebrating Braso as part of The Drum’s Rebel 50 and Block as a driver of the Rebel 50 project, it’s clear that the boldest marketers are those willing to walk away from the industry’s “rules” when those rules diminish creativity, joy and long-term value. Rebellion, in their hands, isn’t anarchy. It’s a discipline. And it might just be the most effective marketing strategy of all.
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